4-[(2-Acetylamino-1-iminoethylthio)acetyl]-2-(diaminomethyleneamino)thiazole hydrobromide → 4-(2-Acetylaminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole

HRID 1491863Notes

Reaction equation

HRID 1491863 reaction equation
Br.[C:2]([NH:5][CH2:6][C:7](=[NH:21])[S:8][CH2:9][C:10]([C:12]1[N:13]=[C:14]([N:17]=[C:18]([NH2:20])[NH2:19])[S:15][CH:16]=1)=O)(=[O:4])[CH3:3]>C(O)C>[C:2]([NH:5][CH2:6][C:7]1[S:8][CH:9]=[C:10]([C:12]2[N:13]=[C:14]([N:17]=[C:18]([NH2:20])[NH2:19])[S:15][CH:16]=2)[N:21]=1)(=[O:4])[CH3:3]

Participants

3

Reactant 1

HCID 189537784-[(2-Acetylamino-1-iminoethylthio)acetyl]-2-(diaminomethyleneamino)thiazole hydrobromide

Product 1

HCID 104023264-(2-Acetylaminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazoleYield 74.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A suspension of 4-[(2-acetylamino-1-iminoethylthio)acetyl]-2-(diaminomethyleneamino)thiazole hydrobromide (11.4 g) in ethanol (100 ml) was refluxed for 2.5 hours. The resulting precipitate was collected by filtration and suspended in water (150 ml). The mixture was alkalized to pH 11 with a saturated aqueous potassium carbonate solution. The resulting precipitate was collected by filtration. Recrystallization from water afforded 4-(2-acetylaminomethylthiazol-4-yl)-2-(diaminomethyleneamino)thiazole (6.36 g).

Workup

  1. temperaturewas refluxed for 2.5 hours
  2. filtrationThe resulting precipitate was collected by filtration
  3. filtrationThe resulting precipitate was collected by filtration
  4. customRecrystallization from water

Sources & evidence

ORD record
ord-c3e1993b409540488714a79014ffdfef
Source dataset
uspto-grants-1994_12
Patent number
US05371097

Reaction notes

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